DE69021034T2 - Verfahren zur Synthese von Benzyltoluol und Dibenzyltoluol mit niedrigem Chlorgehalt. - Google Patents
Verfahren zur Synthese von Benzyltoluol und Dibenzyltoluol mit niedrigem Chlorgehalt.Info
- Publication number
- DE69021034T2 DE69021034T2 DE69021034T DE69021034T DE69021034T2 DE 69021034 T2 DE69021034 T2 DE 69021034T2 DE 69021034 T DE69021034 T DE 69021034T DE 69021034 T DE69021034 T DE 69021034T DE 69021034 T2 DE69021034 T2 DE 69021034T2
- Authority
- DE
- Germany
- Prior art keywords
- benzyltoluene
- oligomers
- toluene
- chloride
- organic products
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 5
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 title abstract description 11
- JBBIOXMOQRDKLN-UHFFFAOYSA-N C(C1=CC=CC=C1)CC1=CC=CC=C1.[Cl] Chemical compound C(C1=CC=CC=C1)CC1=CC=CC=C1.[Cl] JBBIOXMOQRDKLN-UHFFFAOYSA-N 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 77
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims abstract description 28
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 22
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229940073608 benzyl chloride Drugs 0.000 claims abstract description 16
- 238000009833 condensation Methods 0.000 claims abstract description 15
- 230000005494 condensation Effects 0.000 claims abstract description 15
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006298 dechlorination reaction Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- UVROAJFELBNMRA-UHFFFAOYSA-N (1-chloro-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(Cl)CC1=CC=CC=C1 UVROAJFELBNMRA-UHFFFAOYSA-N 0.000 description 3
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- -1 anthraquinone compounds Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/16—Polycyclic non-condensed hydrocarbons containing at least two phenyl groups linked by one single acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
- C07C7/14841—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8917365A FR2656603B1 (fr) | 1989-12-28 | 1989-12-28 | Procedes de synthese de benzyltoluene et dibenzyltoluene a faible teneur en chlore. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69021034D1 DE69021034D1 (de) | 1995-08-24 |
| DE69021034T2 true DE69021034T2 (de) | 1996-03-14 |
Family
ID=9389093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69021034T Expired - Fee Related DE69021034T2 (de) | 1989-12-28 | 1990-12-18 | Verfahren zur Synthese von Benzyltoluol und Dibenzyltoluol mit niedrigem Chlorgehalt. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5202514A (es) |
| EP (1) | EP0435737B1 (es) |
| JP (1) | JPH0651646B2 (es) |
| KR (1) | KR930001323B1 (es) |
| CN (1) | CN1026688C (es) |
| AT (1) | ATE125242T1 (es) |
| CA (1) | CA2033219C (es) |
| DE (1) | DE69021034T2 (es) |
| DK (1) | DK0435737T3 (es) |
| ES (1) | ES2074146T3 (es) |
| FI (1) | FI97221C (es) |
| FR (1) | FR2656603B1 (es) |
| GR (1) | GR3017756T3 (es) |
| IE (1) | IE72094B1 (es) |
| NO (1) | NO174417C (es) |
| PT (1) | PT96383B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4230514A1 (de) * | 1992-02-22 | 1993-08-26 | Huels Chemische Werke Ag | Verfahren zur herstellung von monobenzylierten alkylbiphenylen und deren verwendung |
| JP5009516B2 (ja) * | 2005-09-14 | 2012-08-22 | 出光興産株式会社 | 芳香族化合物の製造方法及びその方法で得られた芳香族化合物 |
| FR3008708B1 (fr) | 2013-07-19 | 2016-09-23 | Arkema France | Composition de fluide dielectrique ou caloporteur |
| CN104513126B (zh) * | 2013-09-26 | 2016-02-03 | 赵朝华 | 一种烷基多苄基甲苯或烷基二苄基甲苯的制备方法和应用 |
| FR3078711B1 (fr) * | 2018-03-08 | 2020-07-31 | Arkema France | Utilisation d'un melange en tant que fluide dielectrique |
| FR3117114B1 (fr) | 2020-12-09 | 2024-04-12 | Arkema France | Formulation liquide pour stockage d’hydrogène |
| FR3117113B1 (fr) | 2020-12-09 | 2024-04-12 | Arkema France | Formulation liquide pour stockage d’hydrogène |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2009224B (en) * | 1977-09-28 | 1982-01-27 | Ici Ltd | Process for the manufacture of benzyl toluenes |
| US4197417A (en) * | 1977-09-28 | 1980-04-08 | Imperial Chemical Industries Limited | Process for the manufacture of o-benzyl toluenes |
| FR2552423B1 (fr) * | 1983-09-23 | 1985-10-25 | Ugine Kuhlmann | Compositions d'oligomeres de polyarylalcanes et leur procede de fabrication |
| CH668709A5 (de) * | 1985-12-06 | 1989-01-31 | Ciba Geigy Ag | Verfahren zur enthalogenierung von polyhalogenierten aliphatischen und aromatischen verbindungen. |
| DE3621175A1 (de) * | 1986-06-25 | 1988-01-07 | Huels Chemische Werke Ag | Verfahren zur enthalogenierung von kohlenwasserstoffoelen |
| FR2620055B1 (fr) * | 1987-09-03 | 1991-05-10 | Atochem | Procede chimique de destruction de produits organiques halogenes |
| SU1498746A1 (ru) * | 1987-09-07 | 1989-08-07 | Предприятие П/Я А-7411 | Способ получени моно- и дибензилтолуолов |
| DE3836780A1 (de) * | 1988-10-28 | 1990-05-03 | Bayer Ag | Verfahren zur herstellung von gegebenenfalls substituierten benzylbenzolen |
-
1989
- 1989-12-28 FR FR8917365A patent/FR2656603B1/fr not_active Expired - Fee Related
-
1990
- 1990-12-18 EP EP90403646A patent/EP0435737B1/fr not_active Expired - Lifetime
- 1990-12-18 DK DK90403646.4T patent/DK0435737T3/da active
- 1990-12-18 ES ES90403646T patent/ES2074146T3/es not_active Expired - Lifetime
- 1990-12-18 DE DE69021034T patent/DE69021034T2/de not_active Expired - Fee Related
- 1990-12-18 AT AT90403646T patent/ATE125242T1/de not_active IP Right Cessation
- 1990-12-26 KR KR1019900021753A patent/KR930001323B1/ko not_active IP Right Cessation
- 1990-12-27 FI FI906413A patent/FI97221C/fi not_active IP Right Cessation
- 1990-12-27 CA CA002033219A patent/CA2033219C/fr not_active Expired - Fee Related
- 1990-12-27 PT PT96383A patent/PT96383B/pt active IP Right Grant
- 1990-12-28 NO NO905631A patent/NO174417C/no not_active IP Right Cessation
- 1990-12-28 IE IE472290A patent/IE72094B1/en not_active IP Right Cessation
- 1990-12-28 US US07/635,673 patent/US5202514A/en not_active Expired - Lifetime
- 1990-12-28 JP JP2416661A patent/JPH0651646B2/ja not_active Expired - Fee Related
- 1990-12-28 CN CN90110008A patent/CN1026688C/zh not_active Expired - Fee Related
-
1995
- 1995-10-17 GR GR950402856T patent/GR3017756T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1052845A (zh) | 1991-07-10 |
| FI97221C (fi) | 1996-11-11 |
| IE904722A1 (en) | 1991-07-17 |
| KR930001323B1 (ko) | 1993-02-26 |
| EP0435737B1 (fr) | 1995-07-19 |
| NO174417B (no) | 1994-01-24 |
| NO905631L (no) | 1991-07-01 |
| CN1026688C (zh) | 1994-11-23 |
| JPH0651646B2 (ja) | 1994-07-06 |
| CA2033219A1 (fr) | 1991-06-29 |
| DK0435737T3 (da) | 1995-11-27 |
| KR910011714A (ko) | 1991-08-07 |
| FR2656603A1 (fr) | 1991-07-05 |
| JPH04139137A (ja) | 1992-05-13 |
| EP0435737A1 (fr) | 1991-07-03 |
| NO905631D0 (no) | 1990-12-28 |
| FI97221B (fi) | 1996-07-31 |
| FI906413A0 (fi) | 1990-12-27 |
| CA2033219C (fr) | 1996-09-24 |
| FI906413A (fi) | 1991-06-29 |
| US5202514A (en) | 1993-04-13 |
| GR3017756T3 (en) | 1996-01-31 |
| FR2656603B1 (fr) | 1993-05-21 |
| PT96383B (pt) | 1998-06-30 |
| ATE125242T1 (de) | 1995-08-15 |
| NO174417C (no) | 1994-05-04 |
| IE72094B1 (en) | 1997-03-12 |
| DE69021034D1 (de) | 1995-08-24 |
| ES2074146T3 (es) | 1995-09-01 |
| PT96383A (pt) | 1991-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PATENTANWAELTE GESTHUYSEN, VON ROHR & EGGERT, 45128 |
|
| 8339 | Ceased/non-payment of the annual fee |